KR102132536B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of Formula 1 and an organic light emitting device including the same.

Description

Polycyclic compound and an organic light emitting device comprising the same{MULTICYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This specification claims the filing date benefit of Korean Patent Application No. 10-2017-0136798 filed with the Korean Patent Office on October 20, 2017, the entire contents of which are incorporated herein.

The present specification relates to a compound and an organic light emitting device including the same.

In the present specification, the organic light emitting device is a light emitting device using an organic semiconductor material, and requires the exchange of holes and/or electrons between the electrode and the organic semiconductor material. The organic light emitting device can be roughly divided into two types according to the operation principle. First, excitons are formed in the organic layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to be used as a current source (voltage source). It is a light emitting device of the form. The second is a light emitting device in which holes and/or electrons are injected into a layer of an organic semiconductor material that interfaces with an electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine. It is known that such an organic light emitting device has characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.

In addition, a host/dopant system may be used as a light emitting material in order to increase color purity and increase light emission efficiency through energy transfer. The principle is that when a small amount of a dopant having a smaller energy band gap and higher luminous efficiency is mixed with the luminescent layer than a host mainly constituting the luminescent layer, exciton generated from the host is transported as a dopant to produce high-efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the above-described organic light-emitting device, a material forming an organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., are supported by stable and efficient materials. Development of new materials continues to be required.

Korea Patent Publication No. 2011-108575

In this specification, a compound and an organic light emitting device including the same are described.

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

X1 and X2 are the same as or different from each other, and each independently O, S, CRaRb or NRc,

Ra, Rb, Rc and R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Sulfide groups; Sulfonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar1 to Ar4 are the same as or different from each other, or each independently a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

n1 and n2 are each an integer of 0 to 3, and when n1 and n2 are each 2 or more, the substituents in parentheses are the same or different from each other,

m1 and m2 are each an integer of 1 to 4, m1+m2≧2, and n1+n2≦6.

In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.

The compound described in this specification can be used as a material for an organic material layer used in an organic light emitting device. The compound according to at least one embodiment exhibits high color purity and long life characteristics, especially in a blue organic light emitting device. In particular, the compounds described herein can be used not only as a light emitting layer, but also as a material for a hole injection layer, a hole transport layer, an electron suppression layer, a hole suppression layer, an electron transport layer, and an electron injection layer.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
Figure 2 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done.
FIG. 3 shows the mass data of Compound 1.
FIG. 4 shows Proton NMR data of Compound 1.

Hereinafter, this specification will be described in more detail.

The present specification provides a compound represented by Formula 1 below. The compound represented by the following Chemical Formula 1 has a strong core structure due to a condensed 6-ring ring, and thus has a long life characteristic, and has a small advantage of low stokes, so it can realize high efficiency and high color reproduction.

[Formula 1]

In Chemical Formula 1,

X1 and X2 are the same as or different from each other, and each independently O, S, CRaRb or NRc,

Ra, Rb, Rc and R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Sulfide groups; Sulfonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar1 to Ar4 are the same as or different from each other, or each independently a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

n1 and n2 are each an integer of 0 to 3, and when n1 and n2 are each 2 or more, the substituents in parentheses are the same or different from each other,

m1 and m2 are each an integer of 1 to 4, m1+m2≧2, and n1+n2≦6.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

In the present specification, when a member is said to be positioned “on” another member, this includes not only the case where one member is in contact with the other member but also another member between the two members.

Examples of the substituent in this specification are described below, but are not limited thereto.

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

Examples of the substituents are described below, but are not limited thereto.

In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

In the present specification, the sulfonyl group means -SO ₂ -R _a , and R _a may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the present specification, the sulfide group means -SR _b , and the R _b may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-ox Tilgi, and the like, but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including the two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, and 2-methyl-biphenylamine Group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthyl amine group, biphenyl phenyl amine group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, benzofluorenyl group, etc., but is not limited thereto. no.

In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups, such as

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heteroatom as a ring group containing at least one of N, O, P, S, Si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridyl group, pyrrol group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, naphthobenzofura Neal group, naphthobenzothiophenyl group,

And the like, but are not limited to these.

In the present specification, a description of the aforementioned heterocyclic group may be applied, except that the heteroaryl group is aromatic.

In the present specification, the description of the aryl group described above may be applied, except that the arylene group is a divalent group.

In the present specification, the description of the heteroaryl group described above may be applied, except that the heteroarylene group is a divalent group.

In this specification, "adjacent" A group may mean a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent located closest in conformation to the substituent, or another substituent substituted on the atom in which the substituent is substituted. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.

In the present specification, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a hydrocarbon ring; Or a heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group except for the non-monovalent.

In the present specification, the description of the aryl group may be applied, except that the aromatic hydrocarbon ring is not monovalent.

In the present specification, the heterocycle is a non-carbon atom, and contains at least one heteroatom, specifically, the heteroatom contains at least one atom selected from the group consisting of N, O, P, S, Si and Se, etc. can do. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.

According to an exemplary embodiment of the present specification, m1 and m2 are each an integer of 1 to 4, m1 + m2 ≥ 2, n1 + n2 ≤ 6.

In another exemplary embodiment, m1 and m2 are 1.

According to an exemplary embodiment of the present specification, the formula 1 may be represented by the following formula (2).

[Formula 2]

In Chemical Formula 2,

X1, X2, R1 to R6, L1, L2, n1, n2 and Ar1 to Ar4 are as defined in Chemical Formula 1.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another exemplary embodiment, L1 and L2 are a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

According to another exemplary embodiment, L1 and L2 are a direct bond; Phenylene group; Biphenylene group; Or a naphthylene group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring. do.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group with 1 or more selected from the group consisting of alkyl groups having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; A fluorenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; A benzofluorenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; A dibenzofuranyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms; A dibenzothiophenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms; A carbazole group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms; A naphthobenzofuranyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms; Or a naphthobenzothiophenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl groups 1 A phenyl group unsubstituted or substituted above; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group; A naphthyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group; A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group; A benzofluorenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group; A dibenzofuranyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group and naphthyl group; A dibenzothiophenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group and naphthyl group; A carbazole group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group and naphthyl group; A naphthobenzofuranyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group, and naphthyl group; Or a naphthobenzothiophenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group, and naphthyl group. , Adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, Ar1 and Ar2 combine with each other to form a substituted or unsubstituted heteroring.

According to another exemplary embodiment, Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted aromatic heterocycle.

In another exemplary embodiment, Ar1 and Ar2 combine with each other to form a substituted or unsubstituted carbazole.

According to another exemplary embodiment, Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted heteroring.

According to another exemplary embodiment, Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted aromatic heterocycle.

In another exemplary embodiment, Ar3 and Ar4 combine with each other to form a substituted or unsubstituted carbazole.

According to an exemplary embodiment of the present specification, the formula 1 may be represented by the following formula 3 or 4.

[Formula 3]

[Formula 4]

In Chemical Formulas 3 and 4,

X1, X2 and R1 to R6 are as defined in Formula 1,

R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar1' to Ar4' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n11 and n12 are each an integer from 0 to 3,

p1 to p4 are each an integer of 0 to 4,

When n11, n12 and p1 to p4 are 2 or more, the substituents in parentheses are the same or different from each other.

According to the exemplary embodiment of the present specification, Ar1' to Ar4' are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ar1' to Ar4' are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another exemplary embodiment, Ar1' to Ar4' are the same as or different from each other, and each independently aryl having 6 to 30 carbon atoms unsubstituted or substituted with 1 or more selected from the group consisting of alkyl groups having 1 to 20 carbon atoms. group; Or a heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Ar1' to Ar4' are the same as or different from each other, and each independently substituted or unsubstituted phenyl group with 1 or more selected from the group consisting of alkyl groups having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; A fluorenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; A benzofluorenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; A dibenzofuranyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms; A dibenzothiophenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms; A carbazole group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms; A naphthobenzofuranyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms; Or a naphthobenzothiophenyl group unsubstituted or substituted with 1 or more selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar1' to Ar4' are the same as or different from each other, and each independently a group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a tert-butyl group. A phenyl group unsubstituted or substituted with one or more selected groups; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group; A naphthyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group; A fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group; A benzofluorenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group; A dibenzofuranyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group and naphthyl group; A dibenzothiophenyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group and naphthyl group; A carbazole group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group and naphthyl group; A naphthobenzofuranyl group unsubstituted or substituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group, and naphthyl group; Or a naphthobenzothiophenyl group substituted or unsubstituted with one or more selected from the group consisting of methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, biphenyl group and naphthyl group. .

According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently O, S, CRaRb, or NRc. The compound represented by Chemical Formula 1 includes O, S, C or N as the central element (X1, X2) in the core structure, whereby a device having a long life property can be obtained when applied to the device.

In another exemplary embodiment, X1 and X2 are O.

In another exemplary embodiment, X1 and X2 are S.

In another exemplary embodiment, X1 and X2 are CRaRb.

In another exemplary embodiment, X1 and X2 are NRc.

In another exemplary embodiment, one of X1 and X2 is S, and the other is O.

According to an exemplary embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted n-butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted n-pentyl group; A substituted or unsubstituted n-hexyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to another exemplary embodiment, Ra and Rb are the same as or different from each other, and each independently a methyl group; Ethyl group; n-propyl group; Isopropyl group; n-butyl group; tert-butyl group; n-pentyl group; n-hexyl group; Phenyl group; Biphenyl group; Or a naphthyl group.

In one embodiment of the present invention, Ra and Rb are methyl groups or phenyl groups.

According to an exemplary embodiment of the present specification, Rc is a substituted or unsubstituted aryl group.

In another exemplary embodiment, Rc is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, Rc is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Rc is an aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Rc is a phenyl group; Biphenyl group; Or a naphthyl group.

In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Sulfide groups; Sulfonyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R1 to R6 are the same as or different from each other, and each independently hydrogen; Cyano group; Sulfide groups; Sulfonyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

이다. According to another exemplary embodiment, R1 to R6 are the same as or different from each other, and each independently hydrogen; Cyano group; Phenyl sulfide group; Phenylsulfonyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted n-butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted carbazole group; or

to be.

이다.In another exemplary embodiment, R1 to R6 are the same as or different from each other, and each independently hydrogen; Cyano group; Phenyl sulfide group; Phenylsulfonyl group; Methyl group; Ethyl group; n-propyl group; Isopropyl group; n-butyl group; tert-butyl group; Diphenylamine group; a phenyl group unsubstituted or substituted with tert-butyl group; Biphenyl group; Naphthyl group; Carbazole; or

to be.

According to an exemplary embodiment of the present specification, the n1 and n2 is 0 or 1.

In another exemplary embodiment, n11 and n12 are 0 or 1.

According to another exemplary embodiment, p1 to p4 are 0 or 1.

According to one embodiment of the present specification, R21 to R24 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, R21 to R24 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, R21 to R24 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R21 to R24 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.

According to another exemplary embodiment, R21 to R24 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, R21 to R24 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted n-butyl group; Or a substituted or unsubstituted tert-butyl group.

According to another exemplary embodiment, R21 to R24 are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; n-propyl group; Isopropyl group; n-butyl group; Or tert-butyl group.

According to an exemplary embodiment of the present specification, the formula 1 is represented by any one of the following formulas 5 to 8.

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Chemical Formulas 5 to 8,

X1, X2, R1 to R4, L1, L2 and Ar1 to Ar4 are the same as defined in Formula 1,

R101 to R108 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Sulfide groups; Sulfonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

s1 to s8 are each an integer of 0 to 3, and when s1 to s8 are each an integer of 2 or more, the substituents in parentheses are the same or different.

According to an exemplary embodiment of the present specification, R101 to R108 are the same as or different from each other, and each independently hydrogen; Cyano group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R101 to R108 are the same as or different from each other, and each independently hydrogen; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted propyl group; Or a substituted or unsubstituted phenyl group.

In another exemplary embodiment, R101 to R108 are the same as or different from each other, and each independently hydrogen; Cyano group; A substituted or unsubstituted methyl group; A substituted or unsubstituted isopropyl group; Or a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, R101 to R108 are the same as or different from each other, and each independently hydrogen; Cyano group; Methyl group; Isopropyl group; Or a phenyl group.

According to one embodiment of the present specification, s1 to s8 are 0 or 1, respectively.

In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Compounds 1 to 72.

The compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later.

For example, the compound of Formula 1 may have a core structure as shown in the following scheme. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art.

<Reaction formula>

B can be synthesized from 2,7-substituted natalene derivative A. Where R is a protecting substituent consisting of alkyl or aryl.

The obtained B can synthesize D through palladium coupling reaction with fluoro compound C. Here, B represents a boronic acid or boronic acid alkyl ester as a boron functional group.

The obtained naphthalene derivative of D can be selectively halogenated at positions 1, 1, or 8 through a halogenation reagent. H can be obtained by converting it to a derivative of desired alkyl, aryl, oxygen, or sulfur using strong base or Grignard reagents or other suitable nucleophilic reagent.

F can be obtained by G using an appropriate de-protecting method, and then H can be obtained by forming a ring under basic conditions.

The obtained H can obtain J through an appropriate amine derivative I and palladium coupling reaction. The obtained J can be purified by column chromatography, recrystallization or sublimation purification to obtain high purity.

The general method described describes the most representative method, and if the reaction is easy, the intermediate reaction can be omitted and synthesized. As an example, there is a palladium coupling reaction with I directly without a protection reaction from A to B.

The above reaction formula describes a synthesis process for an example of the compound represented by Formula 1 in the present specification, and various kinds of compounds represented by Formula 1 can be synthesized through a substituent bonding method and a reaction scheme known in the art. .

In the above scheme, the definitions of L1, L2, Ar1 to Ar4, R1, R2, R5 and R6 are as defined in Formula 1 above.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents to the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure having the above structure.

In addition, by introducing various substituents to the core structure of the structure as described above, it is possible to synthesize a compound having intrinsic properties of the introduced substituents. For example, by introducing into the core structure a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device, a material satisfying the conditions required for each organic material layer can be synthesized. Can.

In addition, the organic light emitting device according to the present invention includes a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, at least one layer of the organic material layer includes the above-described compound, the light emitting layer may include a compound represented by the following formula 1A.

[Formula 1A]

In Formula 1A,

L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

p is an integer from 0 to 6,

When p is 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present specification, L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another exemplary embodiment, the L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanylene group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another exemplary embodiment, the L103 to L106 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenyl group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.

According to another exemplary embodiment, the L103 to L106 are the same as or different from each other, and each independently a direct bond; Or it may be selected from the following structures.

According to an exemplary embodiment of the present specification, L103 is a direct bond.

According to an exemplary embodiment of the present specification, L104 is a phenylene group.

According to an exemplary embodiment of the present specification, L105 and L106 are a direct bond.

In one embodiment of the present specification, R24 is hydrogen; heavy hydrogen; Halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R24 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R24 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R24 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

In another exemplary embodiment, R24 is hydrogen.

According to an exemplary embodiment of the present specification, the p is 0 or 1.

In one embodiment of the present specification, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms; Or a C2-C60 heteroaryl group substituted or unsubstituted with a C2-C60 aryl group or a C2-C60 heteroaryl group.

In another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilol group.

According to another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with an aryl group; A carbazole group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; A furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indole carbazole; Pyridyl group; An isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; A triazine group unsubstituted or substituted with an aryl group; A benzimidazole group unsubstituted or substituted with an aryl group; A benzoxazole group unsubstituted or substituted with an aryl group; A benzothiazole group unsubstituted or substituted with an aryl group; A dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; Xanthene group unsubstituted or substituted with an alkyl group or an aryl group; Or a dibenzosilol group unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with a phenyl group; A carbazole group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Thiophene group unsubstituted or substituted with a phenyl group; A furan group unsubstituted or substituted with a phenyl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group or a phenyl group; Indole carbazole; A pyridyl group unsubstituted or substituted with a phenyl group or a naphthyl group; An isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; A triazine group unsubstituted or substituted with a phenyl group; A benzimidazole group unsubstituted or substituted with a phenyl group; A benzoxazole group unsubstituted or substituted with a phenyl group; A benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; A xanthene group unsubstituted or substituted with a methyl group or a phenyl group; Or a dibenzosilol group unsubstituted or substituted with a methyl group or a phenyl group.

In one embodiment of the present specification, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Or it may be selected from the following structures.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, at least one layer of the organic material layer includes the above-described compound, the light emitting layer may include a compound represented by the formula (1B).

Among the organic material layers of the organic light emitting device of the present specification, a structure of Formula 1B may be included as a material for a host of the light emitting layer.

[Formula 1B]

In Formula 1B,

L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar9 to Ar11 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

q is an integer from 0 to 7,

When q is 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, R25 is hydrogen; heavy hydrogen; Halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

In another exemplary embodiment, R25 is hydrogen.

According to an exemplary embodiment of the present specification, q is 0 or 1.

In one embodiment of the present specification, L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present specification, L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another exemplary embodiment, L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanylene group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another exemplary embodiment, L107 to L109 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenyl group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.

According to another exemplary embodiment, L107 to L109 are the same as or different from each other, and each independently a direct bond; Or it may be selected from the following structures.

In one embodiment of the present specification, L107 to L109 are a direct bond.

In one embodiment of the present specification, Ar9 to Ar11 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently substituted or unsubstituted aryl having 6 to 60 carbon atoms or aryl group having 2 to 60 carbon atoms or aryl group having 2 to 60 carbon atoms. group; Or a C2-C60 heteroaryl group substituted or unsubstituted with a C2-C60 aryl group or a C2-C60 heteroaryl group.

In another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilol group.

According to another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with an aryl group; A carbazole group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; A furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indole carbazole; Pyridyl group; An isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; A triazine group unsubstituted or substituted with an aryl group; A benzimidazole group unsubstituted or substituted with an aryl group; A benzoxazole group unsubstituted or substituted with an aryl group; A benzothiazole group unsubstituted or substituted with an aryl group; A dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; Xanthene group unsubstituted or substituted with an alkyl group or an aryl group; Or a dibenzosilol group unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with a phenyl group; A carbazole group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Thiophene group unsubstituted or substituted with a phenyl group; A furan group unsubstituted or substituted with a phenyl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group or a phenyl group; Indole carbazole; A pyridyl group unsubstituted or substituted with a phenyl group or a naphthyl group; An isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; A triazine group unsubstituted or substituted with a phenyl group; A benzimidazole group unsubstituted or substituted with a phenyl group; A benzoxazole group unsubstituted or substituted with a phenyl group; A benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; A xanthene group unsubstituted or substituted with a methyl group or a phenyl group; Or a dibenzosilol group unsubstituted or substituted with a methyl group or a phenyl group.

In one embodiment of the present specification, Ar9 to Ar11 are the same as or different from each other, and may be independently selected from the following structures.

The organic light-emitting device of the present invention can be manufactured by a conventional manufacturing method and material of an organic light-emitting device, except that one or more layers of organic materials are formed using the compounds described above.

The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer, a layer simultaneously performing hole injection and hole transport, a light emitting layer, an electron transport layer, an electron injection layer, a layer simultaneously performing electron injection and electron transport, and the like as an organic material layer. It can have a structure. However, the structure of the organic light emitting device is not limited to this, and may include a smaller number of organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may include a compound represented by Chemical Formula 1.

In the organic light emitting device of the present invention, the organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include a compound represented by Chemical Formula 1.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

According to another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a dopant in the light emitting layer.

In another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 may include a compound represented by Chemical Formula 1 as a dopant, and may include Chemical Formula 1A or 1B as a host.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a compound represented by Formula 1 as a dopant of the light emitting layer, the compound represented by Formula 1A or Formula 1B as a host of the light emitting layer Included, it can be doped with a compound represented by the formula (1) to 1 to 30wt%. According to another exemplary embodiment, the heterocyclic compound represented by Chemical Formula 1 may be doped at 2 to 20 wt%.

In another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals or metal compounds It may include as a dopant.

As another example, the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and can be used with an iridium-based (Ir) dopant. have.

In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound may be included in the light emitting layer 3.

2 shows an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1 The structure is illustrated. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7 or the electron transport layer 8.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof It can be prepared by depositing an anode to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto, and may have a single layer structure. In addition, the organic material layer has a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, using a variety of polymer materials. Can be prepared in layers.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into an organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection material is a material that can be well injected holes from the anode at a low voltage, and it is preferable that the hole injection material has a high occupied molecular orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer is suitable for a material having high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

As the electron transport material, a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, Also, a compound having excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The hole blocking layer is a layer that prevents the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. The embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.

< Synthetic example >

Synthetic example 1. Synthesis of Compound 1

1) Synthesis of Intermediate 1-1

Intermediate 1-1 was synthesized according to the following scheme.

3,6-dibromonaphthalene-2,7-diol (80.0g, 0.25mol) and (4-chloro-2-fluorophenyl)boronic acid (105.3g, 0.60mol) were added to a 2L flask and 1,4. -Add potassium carbonate (191.2g, 1.38mol) dissolved in dioxane (0.8LL) and water (0.4L). The temperature of the reactor was increased until reflux, and the tetrakistriphenylphosphine palladium catalyst (23.3 g, 0.02 mmol) was diluted with a small amount of 1,4-dioxane and then added. After reflux, the reaction is confirmed and cooled again. This was extracted using water and an ethyl acetate solvent to remove the water layer, and then treated with anhydrous magnesium sulfate and charcoal, filtered using a celite pad, and concentrated to obtain a target product. <Intermediate 1-1> (52 g, yield 50%) was obtained through recrystallization purification with ethyl acetate and hexane.

2) Synthesis of Intermediate 1-2

In <L Intermediate 1-1> (20.0g, 0.05mol) and potassium carbonate (19.9g, 0.14mol) in a 1L flask, add 0.6L of N-methyl-2-pyrrolidone (NMP) and stir. The reaction temperature was raised to 150 ^{° C.} , stirred for one hour, and then cooled to room temperature. After adding 0.3 L of water as a reactant, the mixture was further stirred for one hour, filtered and washed with 0.3 L of normal hexane. After drying with nitrogen, <Intermediate 1-2> rule (15 g, yield 83%) was obtained.

MALDI-TOF MS [M+]=376.0

3) Synthesis of Compound 1

In a 0.5L flask, <Intermediate 1-2> (12.0g, 0.03mol), di-t-butylamine (18.8g, 0.07mmol), sodium t-butoxide (13.8g, 0.14mol) with 0.35L toluene After injection, warm to 130℃. Here, Pd(t-Bu ₃ ) ₂ (0.98 g, 1.91 mmol) was added dropwise as a reactant together with a small amount of toluene. After reaction for about 2 hours, the reaction temperature was cooled to room temperature, and then extracted with an aqueous solution of saturated ammonium chloride and ethyl acetate. The obtained organic layer was treated with activated carbon, anhydrous magnesium, and charcoal, filtered through celite, and concentrated. Recrystallization purification was performed with ethyl acetate and hexane, and dried with nitrogen to obtain <Compound 1> (9.5 g, yield 34%). Mass data of Compound 1 is shown in FIG. 3, and Proton NMR data is shown in FIG. 4.

MS [M+H]=868

Synthetic example 2. Synthesis of Compound 2

Compound 2 was synthesized according to the following scheme.

<Intermediate 1-2> (7.5 g, 0.02 mol) and N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-4-amine in the same manner as in the synthesis of Compound 1 ( <Compound 2> was obtained (9.5 g, yield 34%) using 12.6 g, 0.04 mol).

MS [M+H]=908

Synthetic example 3. Synthesis of Compound 4

Compound 4 was synthesized according to the following scheme.

<Intermediate 1-2> (8.0 g, 0.02 mol) and di([1,1'-biphenyl]-4-yl)amine (14.3 g, 0.05 mol) were used in the same manner as in the synthesis of Compound 1. <Compound 4> was obtained (6.3 g, yield 31%).

Synthetic example 4. Synthesis of Compound 32

1) Synthesis of Intermediate 3-1

Intermediate 3-1 was synthesized according to the following scheme.

In a 0.5L flask, <Intermediate 1-2> (40.0g, 0.106mol) and NBS (N-bromosuccinimide) (20.8g, 0.117mol) were added and chloroform: DMF (dimethylformaldehyde) in a 3:1 ratio After adding 300 mL of the solvent, the temperature was raised from room temperature to 70°C and stirred for 60 hours. After the reaction was completed, it was cooled to room temperature. The solid obtained by filtration was extracted with water and a chloroform solvent to remove the water layer, and then treated with anhydrous magnesium sulfate and charcoal, filtered using a celite pad, and concentrated to obtain a target product. <Intermediate 3-1> (10.5 g, yield 22%) was obtained through recrystallization purification using chloroform and normal hexane.

MS [M+H] = 457

2) Synthesis of Intermediate 3-2

<Intermediate 3-1> (10.0g, 0.22mol) was added to a 0.25L flask, and 29mL of anhydrous tetrahydrofuran (1M THF) was added under a nitrogen atmosphere to lower it to a temperature of -40°C. Here, 24 ml of phenylmagnesium bromide was slowly added thereto, heated to room temperature, and stirred for 24 hours. After the reaction was completed, the reaction solution was extracted with water and chloroform, treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained solid was recrystallized from toluene and normal hexane to obtain <Intermediate 3-2> rule (6.0 g, yield 60%).

MS [M+H] = 454

3) Synthesis of Compound 33

In the same manner as in the synthesis of Compound 1 in Synthesis Example 1, <Intermediate 3-2> (6.0g, 0.13mol) and N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b <Compound 33> was obtained (4.6 g, yield 30%) using ,d]thiophen-3-amine (11.4 g, 0.029 mol).

MS [M+H] = 1164

< Example >

Example One.

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was put in distilled water in which a dispersing agent was dissolved and washed with ultrasonic waves. As a detergent, a product of Fischer Co. was used, and distilled water was used by Millipore Co. Distilled water, which was second filtered as a product filter, was used. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared ITO transparent electrode, HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. Then, the following HT-A 1000 진공 was vacuum-deposited as a hole transport layer, and subsequently HT-B 100 Å was deposited. The light emitting layer was doped with H-A and compound 1 at 2 to 10 wt% as a host, and vacuum deposited to a thickness of 200 Pa. Subsequently, 300-of ET-A and Liq were deposited in a 1:1 ratio, and subsequently, 150 은 thick silver (Ag) 10 wt% doped magnesium (Mg) and 1,000 Å thick aluminum were deposited to form a cathode. Thus, an organic light emitting device was manufactured.

In the above process, the deposition rate of the organic material was maintained at 1 Å/sec, LiF was 0.2 Å/sec, and aluminum was maintained at a deposition rate of 3 Å/sec to 7 Å/sec.

Example 2.

In Example 1, an organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1.

Example 3.

In Example 1, an organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1.

Example 4.

In Example 1, an organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 33 was used instead of Compound 1.

Example 5.

In Example 1, an organic light emitting device was manufactured in the same manner as in Example 1, except that compound H-B was used instead of H-A.

Example 6.

In Example 2, an organic light emitting device was manufactured in the same manner as in Example 2, except that Compound H-B was used instead of H-A.

Example 7.

In Example 3, an organic light emitting device was manufactured in the same manner as in Example 3, except that Compound H-B was used instead of H-A.

Example 8.

In Example 4, an organic light emitting device was manufactured in the same manner as in Example 4, except that compound H-B was used instead of H-A.

Example 9.

In Example 1, an organic light emitting device was manufactured in the same manner as in Example 1, except that compound H-C was used instead of H-A.

Example 10.

In Example 2, an organic light emitting device was manufactured in the same manner as in Example 2, except that compound H-C was used instead of H-A.

Example 11.

In Example 3, an organic light emitting device was manufactured in the same manner as in Example 3, except that compound H-C was used instead of H-A.

Example 12.

In Example 4, an organic light emitting device was manufactured in the same manner as in Example 4, except that compound H-C was used instead of H-A.

< Comparative example >

Comparative example One.

An organic light emitting diode was manufactured according to the same method as Example 1 except for using D-1 instead of Compound 1 in Example 1.

Comparative example 2.

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using D-2 instead of Compound D-1 in Comparative Example 1.

Comparative example 3.

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using D-3 instead of Compound D-1 in Comparative Example 1.

Comparative example 4.

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using D-4 instead of Compound D-1 in Comparative Example 1.

Comparative example 5.

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound H-B was used instead of H-A in Comparative Example 1.

Comparative example 6.

An organic light emitting device was manufactured in the same manner as in Comparative Example 2, except that Compound H-B was used instead of H-A in Comparative Example 2.

Comparative example 7.

An organic light emitting device was manufactured in the same manner as in Comparative Example 3, except that Compound H-B was used instead of H-A in Comparative Example 3.

Comparative example 8.

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound H-C was used instead of H-A in Comparative Example 1.

Comparative example 9.

An organic light emitting device was manufactured in the same manner as in Comparative Example 2, except that Compound H-C was used instead of H-A in Comparative Example 2.

Comparative example 10.

An organic light emitting device was manufactured in the same manner as in Comparative Example 3, except that Compound H-C was used instead of H-A in Comparative Example 3.

Comparative example 11.

An organic light emitting device was manufactured in the same manner as in Comparative Example 4, except that Compound H-C was used instead of H-A in Comparative Example 4.

The driving voltage and luminous efficiency of the organic light-emitting devices of Examples 1 to 12 and Comparative Examples 1 to 11 were measured at a current density of 10 mA/cm ² , and the time to be 95% compared to the initial luminance at a current density of 20 mA/cm ² . (LT95) was measured. The results are shown in Table 1 below.

Example Host Dopant @ 10 mA/cm ² @ 20 mA/cm ² Voltage (V) Efficiency (cd/A) CIE y Life (hr) Example 1 H-A Compound 1 4.3 6.25 0.040 145 Example 2 H-A Compound 2 4.2 6.53 0.042 180 Example 3 H-A Compound 4 4.6 6.30 0.043 165 Example 4 H-A Compound 33 4.4 6.60 0.044 190 Example 5 H-B Compound 1 4.2 6.23 0.040 185 Example 6 H-B Compound 2 4.2 6.50 0.042 190 Example 7 H-B Compound 4 4.4 6.50 0.043 185 Example 8 H-B Compound 33 4.2 6.60 0.044 190 Example 9 H-C Compound 1 4.3 6.75 0.040 220 Example 10 H-C Compound 2 4.3 6.65 0.042 190 Example 11 H-C Compound 4 4.6 6.50 0.043 195 Example 12 H-C Compound 33 4.4 6.60 0.044 200 Comparative Example 1 H-A D-1 4.6 6.10 0.043 140 Comparative Example 2 H-A D-2 4.6 5.20 0.042 130 Comparative Example 3 H-A D-3 4.7 6.10 0.040 120 Comparative Example 4 H-A D-4 4.8 4.20 0.032 60 Comparative Example 5 H-B D-1 4.5 5.80 0.043 130 Comparative Example 6 H-B D-2 4.5 5.00 0.042 110 Comparative Example 7 H-B D-3 4.6 5.75 0.040 105 Comparative Example 8 H-C D-1 4.7 5.90 0.043 135 Comparative Example 9 H-C D-2 4.7 5.30 0.043 115 Comparative Example 10 H-C D-3 4.6 5.75 0.039 85 Comparative Example 11 H-C D-4 4.6 5.30 0.033 70

Examples 1 to 12 using the compound represented by Chemical Formula 1 from Table 1 as a dopant in the light emitting layer, and Comparative Examples 1, 5 and 8 using a pyrene compound; Comparative Examples 2, 6 and 9 using benzofluorene compounds; And it can be seen that the driving voltage of the device is lower than that of Comparative Examples 3, 7 and 10 using the boron-based compound, the efficiency is excellent, and it has long life characteristics. Particularly, Comparative Examples 4 and 11 using compounds (D-4) having the same core structure as the compound represented by Formula 1, but having different center elements included in the core structure, drive voltages of the devices than Examples 1 to 12 herein. It is confirmed that this is high, the efficiency is low, and the lifetime characteristics of the device are reduced by about 51% to 73%.

1: Substrate
2: anode
3: light emitting layer
4: Cathode
5: hole injection layer
6: hole transport layer
7: emitting layer
8: electron transport layer

Claims (15)

Compound represented by the following formula 5 or 8:
[Formula 5]

[Formula 8]

In Chemical Formulas 5 and 8,
X1 and X2 are the same as or different from each other, and each independently O, S or CRaRb,
Ra, Rb and R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Sulfide groups; Sulfonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
R101, R102, R107 and R108 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Sulfide groups; Sulfonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
s1, s2, s7 and s8 are integers from 0 to 3, respectively, and when s1, s2, s7 and s8 are integers of 2 or more, the substituents in parentheses are the same or different. delete delete Compounds represented by any one of the following compounds:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the compound according to any one of claims 1 and 4. Light emitting element. The method according to claim 5,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. The method according to claim 5,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound. The method according to claim 5,
The organic material layer includes an emission layer, and the emission layer includes the compound. The organic light emitting device of claim 5, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or a hole blocking layer includes the compound. The method according to claim 5,
The organic material layer includes a light emitting layer, the light emitting layer is an organic light emitting device comprising a compound represented by the formula (1A):
[Formula 1A]

In Formula 1A,
L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
p is an integer from 0 to 6,
When p is 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 10,
L103 to L106 are the same as or different from each other, and each independently a direct bond; Or an organic light emitting device that is selected from the following structures:

. The method according to claim 10,
Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Or an organic light emitting device that is selected from the following structures:

. The method according to claim 5, The organic layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising a compound represented by the formula (1B):
[Formula 1B]

In Formula 1B,
L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar9 to Ar11 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
q is an integer from 0 to 7,
When q is 2 or more, the substituents in parentheses are the same or different from each other. The method according to claim 13,
L107 to L109 are the same as or different from each other, and each independently a direct bond; Or an organic light emitting device that is selected from the following structures:

. The method according to claim 13,
The Ar9 to Ar11 are the same as or different from each other, and each independently an organic light emitting device selected from the following structures:

.

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